Abstract

A new route for the synthesis of tetrahydrocortisone 3-glucuronide has been developed with cortisone acetate as a starting material. The key step was using lithium tri-tert-butoxyaluminum hydride to reduce the C-3 carbonyl group of 5β-dihydrocortisone acetate (8) to provide 3α-5β-tetrahydrocortisone acetate (5). Then, Koenig–Knorr method was used for glycosylation with glycosyl bromide as the donor, cadmium carbonate as promoter and 4Å molecular sieves as dehydrating agent to give high yield of the desired product. The new route is shorter and gives higher yield than that reported in the literature.

中文翻译：

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四氢可的松3-葡糖苷酸的新合成

摘要

以醋酸可的松为起始原料，开发了一条合成四氢可的松 3-葡糖苷酸的新路线。关键步骤是使用氢化三叔丁氧基铝锂还原 5 β - 二氢可的松醋酸酯 (8) 的 C-3 羰基，得到 3 α -5 β -醋酸四氢可的松 (5)。然后，采用 Koenig-Knorr 法进行糖基化，以溴化糖为供体，碳酸镉为促进剂，4Å 分子筛为脱水剂，得到所需产物的高收率。与文献报道的相比，新路线更短，产率更高。